I feel like there are a few things to note here:
1) I like the song. I like it a lot. I’m surprised that this is the first time I’ve heard of it. It’s goofy, silly, pointed, and fun.
2) It’s safe to bet that there are other rappers who’ve mined this territory but not received the attention for it that Macklemore and Ryan Lewis have due to lack of mirth, hook, or just straight up because these dudes are white and from the Pac NW, so that’s still a novelty thing going on.
3) With #2’s caveat in mind, this is pretty much a classic and well-used trope: take the things used against you by mass culture — in this case, the fetishizing of the latest fashions and the askance glares given to thrift stores — and posit them as virtues. It’s a kind of pride reclamation.
4) “I probably shoulda washed this, it smells like R. Kelly’s sheets / PISSSSSSSSSSSSSS.” I’m still laughing.
5) I have friends who should bump this song — particularly ladies, especially my girlfriend — continuously because they live in thrift shops to save a few bucks here and there.
6) I am so old in pop culture time now. This song was released in October and I just found out about it.
7) Macklemore is Seattle-proud, but dude is a Portlandia cameo waiting to happen.